Antibacterial compounds from the stem barks of Garcinia cowa Ittipon Siridechakorn PhD. Program in Applied Chemistry School of Science, Mae Fah Luang University

Introduction Asia Africa 2

Garcinia cowa  Family: Clusiaceae  Thai name: Cha Muang ( ชะมวง )  Commonly found in tropical Asia, Africa, and Polynesia  Rich source of molecules exhibiting a wide pharmacological profile  Xanthones, flavanone, and acylphloroglucinol derivative 3

Literature Reviews Mahabusarakhum et al., 2005 (G. cowa latex) 4

Literature Reviews Panthong et al., 2006 (G. cowa fruits) Antibacterial activities, S. aureus ATCC and MRSA SK1 5

Literature Reviews Winnie et al., 2010 (G. cowa twigs) 6

Literature Reviews 7 Winnie et al., 2010 (G. cowa twigs) cont.

Plant Material The stem barks of G. cowa were collected from Nong khai Province of Thailand in April The plant was identified by Mr. James Maxwell Herbarium of Chiang Mai University and the specimen (MFU- NPR0014) was deposited at Natural Products Research Laboratory, School of Science, Mae Fah Luang University. 8

Extraction and Isolation 9

GC1 Stem barks of G. cowa ( g) Chromatography techniques Recrystallization GC2 GC3 GC4 GC5 GC6 GC7 GC compounds GC9 GC10 GC11 GC12 GC13 GC14 GC15 GC16 GC17

Structure Elucidation 11

1 H NMR spectrum of Garciniacowol (CDCl 3 at 400 MHz) δ 6.27 (1H, s) δ 2.20 (3H, s) 13 C NMR spectrum of Garciniacowol (CDCl 3 at 400 MHz) O-C Sp 2 Sp 3 27 Carbons 12

HMBC spectrum of garciniacowol (CDCl 3 at 400 MHz) 13

HMBC spectrum of garciniacowol (CDCl 3 at 400 MHz) 14

1 H NMR spectrum of garciniacowol (CDCl 3 at 400 MHz) δ 1.71 (2H, m) δ 2.35 (1H, m) δ 2.17 (1H, m) 15

HMBC spectrum of garciniacowol (CDCl 3 at 400 MHz) 16

17 HMBC spectrum of garciniacowol (CDCl 3 at 400 MHz) 1 H NMR spectrum of garciniacowol (CDCl 3 at 400 MHz) 17

Garciniacowol ESI-TOF-MS: m/z [M+H] + (calcd for C 54 H 79 O 4, ) parvifoliol F Rukachaisirikul, et al. Tetrahedron 2006;62:

1 H NMR spectrum of garciniacowone (CDCl 3 at 400 MHz) δ 6.44 (1H, s) δ (1H, s) δ 2.76 (1H, dd, J=15.2, 7.2 Hz) δ 2.79 (1H, dd, J=15.2, 8.4 Hz) δ 3.35 (1H, m) 13 C NMR spectrum of garciniacowone (CDCl 3 at 400 MHz) C=O O-C Sp 2 Sp 3 28 Carbons 19

1 H NMR spectrum of garciniacowone (CDCl 3 at 400 MHz) 13 C NMR spectrum of garciniacowone (CDCl 3 at 400 MHz) C=O O-C Sp 2 Sp 3 27 Carbons 20

HMBC spectrum of garciniacowone (CDCl 3 at 400 MHz) δ 2.47, 2.23 δ

HMBC spectrum of garciniacowone (CDCl 3 at 400 MHz) δ 2.92,

Structure Elucidation NOE correlation δ 2.65 δ 3.35 δ

1 H NMR spectrum of garciniacowone (CDCl 3 at 400 MHz) 13 C NMR spectrum of garciniacowone (CDCl 3 at 400 MHz) Garciniacowone [  ] D (c = 0.043, MeOH) ESI-TOF-MS: m/z [M+H] + (calcd for C 28 H 34 O 6, ) 24

GC3 GC4 GC5 GC6 GC7 GC8 25 GC9 GC10 GC11 GC12 GC13 GC14 GC15 GC16 GC17 15 known compounds

Compound MIC (µg/mL) MRSA-SK1S. aureus Garciniacowolinactive Garciniacowone22 Parvifoliol F128inactive α-Mangostine16128 β-Mangostine16inactive Cowaxanthone16 Norcowanin168 Cowanin432 Cowanol28 Cowagarcinone Binactive Cowagarcinone D128inactive Cowagarcinone E8inactive Fuscaxanthone Ainactive Fuscaxanthone Cinactive Cowaxanthone D128inactive Vancomycin10.25 Gentamycinnot tested Cowanin Cowanol Cowagarcinone E Garciniacowone Antibacterial activity 26

Conclusion 27

Acknowledgement Asst. Prof. Dr. Surat Laphookhieo, MFU Dr. Monthon Norsangsri, QBG Assoc. Prof. Dr. Uma Prawat, PKRU Dr. Thunwadee Ritthiwigrom, CMU Mr. Nitirat Chimnoi, CRI Assoc. Prof. Dr. Suchada Chantrapromma, PSU